Literature DB >> 33322249

A Facile Semisynthesis and Evaluation of Garcinoic Acid and Its Analogs for the Inhibition of Human DNA Polymerase β.

Satheesh Gujarathi1, Maroof Khan Zafar2, Xingui Liu1, Robert L Eoff2, Guangrong Zheng1,3.   

Abstract

Garcinoic acid has been identified as an inhibitor of DNA polymerase β (pol β). However, no structure-activity relationship (SAR) studies of garcinoic acid as a pol β inhibitor have been conducted, in part due to the lack of an efficient synthetic method for this natural product and its analogs. We developed an efficient semi-synthetic method for garcinoic acid and its analogs by starting from natural product δ-tocotrienol. Our preliminary SAR studies provided a valuable insight into future discovery of garcinoic acid-based pol β inhibitors.

Entities:  

Keywords:  DNA polymerase β; garcinoic acid; semi-synthesis; structure-activity-relationship; δ-tocotrienol

Year:  2020        PMID： 33322249      PMCID： PMC7763917          DOI： 10.3390/molecules25245847

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  20 in total

1.  A stereocontrolled synthesis of delta-trans-tocotrienoloic acid.

Authors:  David J Maloney; Sidney M Hecht
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

2.  Synthesis of (2R,8' S,3' E)-δ-tocodienol, a tocoflexol family member designed to have a superior pharmacokinetic profile compared to δ-tocotrienol.

Authors:  Xingui Liu; Satheesh Gujarathi; Xuan Zhang; Lijian Shao; Marjan Boerma; Cesar M Compadre; Peter A Crooks; Martin Hauer-Jensen; Daohong Zhou; Guangrong Zheng
Journal:  Tetrahedron       Date:  2016-05-12       Impact factor: 2.457

3.  Enhanced expression and activity of DNA polymerase beta in human ovarian tumor cells: impact on sensitivity towards antitumor agents.

Authors:  V Bergoglio; Y Canitrot; L Hogarth; L Minto; S B Howell; C Cazaux; J S Hoffmann
Journal:  Oncogene       Date:  2001-09-27       Impact factor: 9.867

4.  Deuteration of the farnesyl terminal methyl groups of δ-tocotrienol and its effects on the metabolic stability and ability of inducing G-CSF production.

Authors:  Xingui Liu; Zhengya Gao; Qiang Fu; Lin Song; Peiyi Zhang; Xuan Zhang; Howard Hendrickson; Peter A Crooks; Daohong Zhou; Guangrong Zheng
Journal:  Bioorg Med Chem       Date:  2020-04-08       Impact factor: 3.641

Review 5.  Is there a link between DNA polymerase beta and cancer?

Authors:  Daniela Starcevic; Shibani Dalal; Joann B Sweasy
Journal:  Cell Cycle       Date:  2004-08-29       Impact factor: 4.534

6.  Irreversible inhibition of DNA polymerase β by small-molecule mimics of a DNA lesion.

Authors:  Dumitru Arian; Mohammad Hedayati; Haoming Zhou; Zoe Bilis; Karen Chen; Theodore L DeWeese; Marc M Greenberg
Journal:  J Am Chem Soc       Date:  2014-02-11       Impact factor: 15.419

7.  Semisynthetic and Natural Garcinoic Acid Isoforms as New mPGES-1 Inhibitors.

Authors:  Khaled Alsabil; Sorphon Suor-Cherer; Andreas Koeberle; Guillaume Viault; Alexis Lavaud; Veronika Temml; Birgit Waltenberger; Daniela Schuster; Marc Litaudon; Stefan Lorkowski; René de Vaumas; Jean-Jacques Helesbeux; David Guilet; Hermann Stuppner; Oliver Werz; Denis Seraphin; Pascal Richomme
Journal:  Planta Med       Date:  2016-06-10       Impact factor: 3.352

8.  Bleomycin-induced DNA repair synthesis in permeable human fibroblasts: mediation of long-patch and short-patch repair by distinct DNA polymerases.

Authors:  J A DiGiuseppe; S L Dresler
Journal:  Biochemistry       Date:  1989-11-28       Impact factor: 3.162

9.  The vitamin E derivative garcinoic acid from Garcinia kola nut seeds attenuates the inflammatory response.

Authors:  Maria Wallert; Julia Bauer; Stefan Kluge; Lisa Schmölz; Yung-Chih Chen; Melanie Ziegler; Amy K Searle; Alexander Maxones; Martin Schubert; Maria Thürmer; Helmut Pein; Andreas Koeberle; Oliver Werz; Marc Birringer; Karlheinz Peter; Stefan Lorkowski
Journal:  Redox Biol       Date:  2019-03-12       Impact factor: 11.799

10.  Garcinoic Acid Is a Natural and Selective Agonist of Pregnane X Receptor.

Authors:  Desirée Bartolini; Francesca De Franco; Pierangelo Torquato; Rita Marinelli; Bruno Cerra; Riccardo Ronchetti; Arne Schon; Francesca Fallarino; Antonella De Luca; Guido Bellezza; Ivana Ferri; Angelo Sidoni; William G Walton; Samuel J Pellock; Matthew R Redinbo; Sridhar Mani; Roberto Pellicciari; Antimo Gioiello; Francesco Galli
Journal:  J Med Chem       Date:  2020-03-20       Impact factor: 7.446
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